Benzoic acid, 4-(allyloxy)-3,5-dichloro- → 1-[2-(4-Allyloxy-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 900629

Reaktionsgleichung

Reaktionsgleichung von HRID 900629
C(OC1C(Cl)=CC(C(O)=O)=CC=1Cl)C=C.[CH2:16]([O:23][CH:24]1[CH:28]([NH:29][C:30]([CH:32]2[CH2:36][CH2:35][CH2:34][N:33]2[C:37](=[O:55])[CH:38]([NH:40][C:41](=[O:54])[C:42]2[CH:47]=[C:46]([Cl:48])[C:45]([O:49][CH2:50][CH:51]=[CH2:52])=[C:44]([Cl:53])[CH:43]=2)[CH3:39])=[O:31])[CH2:27][C:26](=[O:56])[O:25]1)[C:17]1C=CC=CC=1>>[CH2:16]([O:23][CH:24]1[CH:28]([NH:29][C:30]([CH:32]2[CH2:36][CH2:35][CH2:34][N:33]2[C:37](=[O:55])[CH:38]([NH:40][C:41](=[O:54])[C:42]2[CH:43]=[C:44]([Cl:53])[C:45]([O:49][CH2:50][CH:51]=[CH2:52])=[C:46]([Cl:48])[CH:47]=2)[CH3:39])=[O:31])[CH2:27][C:26](=[O:56])[O:25]1)[CH3:17]

Komponenten

3

Edukt 2

HCID 38951Benzoic acid, 4-(allyloxy)-3,5-dichloro-HCID 229774861-[2-(4-Allyloxy-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

Produkt 1

HCID 229774871-[2-(4-Allyloxy-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amideAusbeute 65 %

Versuchsvorschrift

Prepared from 109 and 4-allyloxy-3,5-dichloro-benzoic acid following the method used in the synthesis of 82 to give the title compound as a white solid (228 mg, 65%). 1H-NMR (500 MHz, CD3OD) δ 1.10-1.30 (m, 4H), 1.32-1.52 (m, 3H), 1.63-2.31 (m, 4H), 2.41-2.50 (d, 0.5H), 2.52-2.61 (dd, 0.5H), 2.67-2.81 (m, 0.5H), 2.94-3.05 (dd, 0.5H), 3.47-3.96 (m, 4H), 4.21-4.81 (m, 5H), 5.22-5.32 (m, 1H), 5.35-5.49 (m, 1.5H), 5.55-5.63 (m, 0.5H), 6.06-6.21 (m, 1H), 7.90 (s, 2H). Analytical HPLC (mixture of 2 diastereomers) 12.56 min. LC-MS (ES+) m/e=542.3(MH+)

Quellen und Nachweise

ORD-Eintrag
ord-4ae4970d7adc4ee89a19b266e244d3cf
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07358273B2

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